4-((3-((Tert-butyldimethylsilyl)oxy)phenyl)(hydroxy)methyl)-N,N-diethylbenzamide → 4-(3-((tert-butyldimethylsilyl)oxy)benzoyl)-N,N-diethylbenzamide

Participants

Reaction Steps

Pyridinium chlorochromate (46.5 g, 0.216 mol) was added to a solution of 4-(3-(tert-butyldimethylsilyloxy)-α-hydroxybenzyl)-N,N-diethylbenzamide (44.6 g, 0.108 mol) from Example 11 in 600 mL dichloromethane at 0° C. The solution was stirred overnight at room temperature and filtered through Celite. The filtrate was concentrated to a volume of 150 mL and purified by chromatography on silica gel with ethyl acetate (5-40%) in hexane to give 29.4 g (66%) of 4-(3-((tert-butyldimethylsilyl)oxy)benzoyl)-N,N-diethylbenzamide as a white solid.

Provenance & Evidence